Biography Wynter probably served an apprenticeship on one of his father’s ships, perhaps in the expedition to the west coast of Ireland in 1580, but it is not until 1585 that his documented career begins. In September of that year, in command of the Aid, he took part in Drake’s voyage to the West Indies. The expedition put in at Vigo in Spain on the outward voyage, and Wynter’s letter from there to Walsingham was the last that anyone in England heard of the ships until their return in July 1586. Wynter was prominent in the capture of Cartagena, apparently being so anxious to take part personally in the fight that he temporarily exchanged command of his ship for that of a company of soldiers. The expedition later plundered the coast of Florida and returned home with booty worth £60,000.3

When it became apparent that there was no immediate prospect of further excitement at home, Wynter determined to seek it on the Continent. In August 1587 he wrote from Bergen-op-Zoom asking Walsingham to secure him the necessary permission:

Because I despair of any new putting again into the field this year, I am resolved to repair with all speed to the King of Navarre, who, as I hear, useth such gentlemen as come unto him honourably ... I am resolved to live in the wars for a time, or else to travel for a year or two. He ends by recording that he left his father ‘most naturally affected towards me’. Judging by a brief reference in a subsequent letter, Wynter obtained the necessary permission and found the service he had been seeking in the Low Countries. It was quite natural, however, that he should return home the following spring when the threat of a Spanish offensive against England became more real. His role in the naval engagement against the Armada is unrecorded; probably he served on his father’s ship. On 17 Aug., some time after the Spanish fleet had been scattered, he dined at Dover with Lord Henry Seymour and Maurice of Nassau, and a week later sent Walsingham the latest information to reach that port. Sailors from Dunkirk had told him that Parma, commander of the Spanish invasion forces in the Netherlands, had fled towards Brussels and had ordered his ships to be unloaded. It was rumoured that the Spanish fleet was somewhere off Orkney. Wynter ended his letter, typically, by telling Walsingham that he was ‘resolved to follow the wars’ and asked to be remembered ‘if there happen any occasion that forces, either of foot or horse, should be employed’.4

Between these periods of active service, Wynter passed his time in London and Gloucestershire. His first appearance in Parliament, for the Cornish borough of Newport, was no doubt due to his father’s friendship with the Grenvilles, the leading local family. In December 1588, just before he succeeded his father, he was elected to one of the Gloucestershire county seats. Next, he set off ‘to pass into France to see the manner of service there’, but fell into the hands of the wife of the governor of Eu and Tréport who, ‘coming aboard in ye haven, took me away’, an obscure episode which cost Wynter four years of captivity, for her husband sold him to Mendoza, the Spanish ambassador in France.5 Wynter wrote to Walsingham from Amiens in October 1589, reporting that he had been well treated, but he pressed for the Queen to arrange his release. His idea was that he should be exchanged for Don Pedro de Valdes, a Spanish nobleman who had been captured during the Armada campaign. By the following February he had been transferred to Antwerp castle, and was not so optimistic about his imminent freedom. It had been reported to him that Parma would only exchange him for all Spanish prisoners in England and Holland, an impossible suggestion, as Wynter fully realised. He was also worrying about his relatives and estates at home. Someone had brought a lawsuit against him, and one of his young brothers still needed supervision. Wynter clearly regarded Walsingham as his principal friend in high places, and implored him to look into these matters, but the secretary could only have received these pleas just before his death. The negotiations for Wynter’s release dragged on for months, even years, and resignation turned to despair. Eventually the Privy Council agreed in principle to the exchange of Valdes for Wynter. By the summer of 1591 the two men had, by frequent correspondence, become quite well known to each other. Valdes apologised to Mondragon, governor of Antwerp castle, when Wynter tried to escape, promising him he would not do it again, and urged him not to punish his charge as he, Valdes, would suffer also. The negotiations at length failed again because the Queen, in spite of a desperate plea from Wynter to Burghley in 1591, decided that Valdes, who had been one of the principal Armada commanders, was too important to be exchanged for a relatively unknown captain. The Council, in a tactfully worded letter, told Wynter the bad news. At this stage some of his friends, particularly Richard Drake, intervened and persuaded him to pay for his own ransom. At last, in the spring of 1593, his release was obtained. Wynter’s return home did not prove to be a happy one. He discovered that Drake, in order to secure his freedom, had undertaken that Wynter should pay for Valdes’s ransom also. His disgust was natural, because Valdes had been living at Drake’s house and some of the ransom money would go to Wynter’s supposed friend. He refused to meet this payment, much to the annoyance of Cecil and the Queen, who was angry that Drake, one of her equerries, had been spoken of scornfully. One can sympathize with the strongly worded letter which Wynter wrote to Cecil in reply to the charges:

Judge, I beseech you, whether after almost four years of barbarous imprisonment, after the racking me with infinite devices to pay £4,500 for my ransom and other charges, after the spending the sweetest time of my youth in all melancholy (in all which Mr. Drake hath been the principal meddler), if after all this, out of my justeth griefs I have perchance breathed some words only of choler, which otherwise might have burst out more violently.6 Though still in his early thirties Wynter had now lost his thirst for action. He retired to his home, the White Cross, at Lydney, and busied himself with the management of his estates and other enterprises, such as the establishment of iron furnaces in the Forest of Dean. Though he remained on the commission of the peace, he would undertake no extra local duties, and asked to be excused serving as sheriff in 1595. It may have been his marriage to a daughter of the Earl of Worcester that brought him back to London and the court. He served again as knight of the shire for Gloucestershire in 1601, and as such he could have served on committees dealing with the order of business, 3 Nov., and monopolies, 23 Nov. Wynter was knighted by the Queen at Greenwich, and served as a canopy bearer at her funeral.7

He died 3 Mar. 1619. The heir was his son John, who vigorously defended his house against parliamentary soldiers. Nothing is known of Wynter’s religious views, but in the next generation the family was Catholic.8